Peter Klaven (Paul Rudd), a successful Los Angeles real estate agent, sets out to find a male friend close enough to serve as his Best Man after getting engaged to Zooey Rice (Rashida Jones). He embarks on a series of awkward "man-dates" with various men, including Sydney Fife (Jason Segel), an investor who becomes his unlikely best friend. As Peter and Sydney's friendship deepens, it strains their relationship with Zooey, leading to a dramatic confrontation that ultimately brings the trio together at the wedding.
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